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Heterocyclic compounds and uses thereof

a technology of heterocyclic compounds and compounds, applied in the field of heterocyclic compounds, can solve the problems of mitotic entry and replication of small-sized yeasts that are not ready to matur

Pending Publication Date: 2022-06-02
GIRAFPHARMA LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes a new compound, called a compound of Formula I, and its salt, which can be used to treat cancer. The compound can also be used to inhibit a protein called Wee1 in cells. The patent also describes pharmaceutical compositions containing the compound and a carrier or excipient, as well as the use of the compound for making a medicament for cancer treatment. Overall, the patent provides a new compound with potential cancer treatment effects.

Problems solved by technology

Wee1 was first identified in fission yeast, where Wee1 deficiency resulted in premature mitotic entry and replication of smaller-sized yeast.

Method used

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  • Heterocyclic compounds and uses thereof
  • Heterocyclic compounds and uses thereof
  • Heterocyclic compounds and uses thereof

Examples

Experimental program
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examples

Synthetic Examples

example s-1

f 2-isopropyl-1-(1-isopropyl-1H-pyrazol-4-yl)-6-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (Compound No. 1.1)

[0150]

[0151]Step-1: Synthesis of 1-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole: To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.0 g, 10.30 mmol, 1.0 eq) in DMF (30 mL) was added 2-iodopropane (2.45 mL, 15.46 mmol, 1.5 eq) and Cs2CO3 (5.36 g, 16.48 mmol). The reaction mixture was heated at 90° C. for 16 h. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (250 mL×2). The combined organic layers were washed with water (250 mL) and brine solution (250 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-40% EtOAc in hexane] to afford the desired compound (1.5 g, 61.72%) as brown solid. LCMS: 237.2 ...

example s-2

f 2-isopropyl-1-(6-(1-methoxy-2-methylpropan-2-yl)pyridin-2-yl)-6-((1,2,3,4-tetrahydroisoquinolin-7-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (Compound No. 1.2)

[0155]

[0156]Step-1: Synthesis of 2-(6-bromopyridin-2-yl)-2-methylpropanoic acid: To a solution of 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (1.5 g, 6.17 mmol, 1.0 eq) in methanol (20 mL) was added 1 N NaOH (20 mL) and the reaction mixture was heated at 100° C. overnight. Progress of the reaction was monitored by TLC analysis. After completion of the reaction, solution was acidified with 2M HCl and the product was extracted into ethyl acetate. Organic layer was dried over sodium sulfate and concentrated to give the desired product (1.2 g, 80.0%) as white solid. LCMS: 243.9 [M+1]+.

[0157]Step-2: Synthesis of 2-(6-bromopyridin-2-yl)-2-methylpropan-1-ol: To a solution of 2-(6-bromopyridin-2-yl)-2-methylpropanoic acid (1.22 g, 5.0 mmol, 1.0 eq) in dry THF (20 mL) was added sodium borohydride (370 mg, 10 mmol, 2.0...

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Abstract

Heterocyclic compounds as Wee1 inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]This application is a national stage application under 35 U.S.C. § 371 of International Application No. PCT / US2020 / 027305, filed internationally on Apr. 8, 2020, which claims priority to U.S. Provisional Application No. 62 / 831,672, filed on Apr. 9, 2019, the contents of which are incorporated herein by reference in their entirety.FIELD OF THE INVENTION[0002]This disclosure relates generally to therapeutics engaged in inhibition of the DNA damage checkpoint kinase, Wee1, which potentiates genotoxic chemotherapies by abrogating cell-cycle arrest and proper DNA repair. The invention also provides pharmaceutically acceptable compositions comprising compounds of the present invention and methods of using said compositions in the treatment of diseases associated with this pathway.BACKGROUND OF THE INVENTION[0003]Wee1 is a tyrosine kinase that phosphorylates and inactivates Cdc2 and is involved in G checkpoint signaling. More particularly, Wee1 i...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D471/04A61K31/519A61K45/06A61P35/00
CPCC07D471/04A61P35/00A61K45/06A61K31/519C07D487/04
Inventor CHAKRAVARTY, SARVAJITPHAM, SON MINHKANKANALA, JAYAKANTHPUJALA, BRAHMAMSONI, SANJEEVJAISWAL, PUJAPALVE, DEEPAKKUMAR, VARUN
Owner GIRAFPHARMA LLC
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